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Twenty years after starting
1-800-Got-Junk?, CEO Brian Scudamore took a sabbatical.
Confident that his crackerjack COO, who had been on the job for
10 months, would keep things thriving while he was away,
Scudamore headed off to cooking school in Italy. "I was very
grateful to her that I was able to get away for five weeks," he
says.

But it didn't take long after his return for Scudamore to sense
that all was not well. To his horror, he realized that the COO
had overspent company funds to near bankruptcy, had been trying
to turn his team against him and was scheming to oust him.

Which brings us to the first rule of vacation planning: Make sure
you have a team you can trust. Leaving one's business to others,
even for just a few days, can fill an entrepreneur with anxiety.

"In the early years, I felt the weight of the world on my
shoulders and believed that no one could keep the company going
during my absence," says Todd Greene, CEO of HeadBlade, a Culver
City, Calif.-based shaving-product company. "As a result, I
hardly ever went away, and when I did it was not enjoyable."

Be stealthy. Edward Gilhuly, president of Left
Communication, has learned that letting staff and clients know
he's going away can provoke unnecessary anxiety and suddenly
push back-burner projects to the fore. "I've found it's
sometimes better to slip away with stealth but stay connected,"
he says. "Not long ago I spent a week at surf camp in Costa
Rica. No work-related contacts ever knew, as I stayed in touch
like normal with e-mail and phone. Maybe even more than usual."

Keep an eye on things. Todd Greene, CEO of
HeadBlade, remains connected even when out of the office,
relying on smartphone apps to watch over his site and his
employees. "I can check the site performance with Google
Analytics," he says. "I can log into the site to fix any
problem or update. I can access financials, credit cards and
bank info. I get e-mails, texts, faxes. I can view my desktop.
Security cameras remotely allow 24/7 surveillance."

Keep talking. Chocolate Lab Apps' Elaine
Henley has "fallen in love with Voxer. It's a
walkie-talkie-style app that works so well when communicating
with your team."

Pre-plan communication. Dhana Cohen,
co-founder of the Women Inventorz Network, suggests that before
a trip, you schedule e-mails to go out to any lists you
maintain, "keeping you present and appearing to be working even
if you take an afternoon on a beach." --S.D.

Business trips or vacations can be much less terrifying if one
plans ahead. Now, Greene says, "before I leave on a trip, we have
an officewide meeting and review everyone's objectives while I'm
away. We establish the chain of command. At all times there has
to be someone in charge who is accountable. I also sign a
specific number of checks that go into the safe in case emergency
purchases are approved and cannot be put on a credit card. One
person is authorized to use the credit card, with a set limit."

Though a few business owners choose to cut off all contact with
work when they're away, most stay in touch but allow their teams
more autonomy than usual. "I use trackers in Google Drive that I
ask my team to update daily," says Elaine Heney, CEO of
Tipperary, Ireland-based Chocolate Lab Apps. "I can log on to
these any time and see a detailed status of all my apps. I also
like to get two weekly e-mail status reports from my manager,
with the status of each app and a list of issues at the end. Both
of these mean I only need to contact my manager if an issue
arises."

Sabina Gault, CEO of Konnect PR in Los Angeles, is accessible to
her staff at all times. "PR is an unpredictable industry," she
says. "No matter how prepared you are, handling crisis
communication is no fun." When on vacation, Gault does step back
a bit. "I don't check on anything small," she says. "My team
knows to handle everything." Her team also knows they can call
when they need her input, such as when dealing with an unhappy
client. "They might call and say, 'Here's what we think. Here's
what we would say. Are you comfortable with this?'"

It took some time, but even Scudamore is back to being
comfortable when he's away from 1-800-Got-Junk?. In fact, he
still prefers to go dark while on vacation, going so far as to
have his assistant change his e-mail password so he can't check
in.

After returning from his Italian sabbatical, he fired the
disloyal COO and several other people and pulled his company out
of its tailspin. Now he maintains his position as the "vision
guy" and has a loyal COO. "A CEO has to have a second in command
that they trust with their life," he points out. "Someone that
you can turn over your keys to."